2-Bromopropane → 3-Methyl-2-(2-naphthyl)butyronitrile

HRID 1071606Notes

Reaction equation

HRID 1071606 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][C:12]#[N:13].Br[CH:15]([CH3:17])[CH3:16].[OH-].[K+]>CS(C)=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl-].[Na+].O>[CH3:16][CH:15]([CH3:17])[CH:11]([C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1)[C:12]#[N:13]

Participants

7

Reactant 3

HCID 63582-BromopropaneHCID 14797Potassium HydroxideHCID 820082-Naphthylacetonitrile

Product 1

HCID 223937393-Methyl-2-(2-naphthyl)butyronitrileYield 64.6%

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 679Dimethyl SulfoxideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

3.00 g (17.9 mmol) of 2-naphthylacetonitrile was dissolved in 10 ml of dimethyl sulfoxide, and 2.43 g (19.7 mmol) of 2-bromopropane, 330 mg (0.90 mmol, cat) of tetra-n-butylammonium iodide and 10 ml of 50% potassium hydroxide were successively added thereto. After completion of the reaction, brine was added, and the mixture was extracted with ether. The organic layer was washed with brine, dried over magnesium sulfate and evaporated, to give a crude product. The crude product was subjected to 150 g of silica gel (ethyl acetate:hexane=1:10), to give 2.42 g (11.6 nmol, 64.6%) of the title compound as a yellow oil.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ether
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customto give a crude product

Sources & evidence

ORD record
ord-de92b22fc5124d0eb36d9b9a5af07a2e
Source dataset
uspto-grants-2005_06
Patent number
US06906072B1

Reaction notes

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